NP-MRD: Showing NP-Card for 10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione (NP0319215)

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Record Information

Version

2.0

Created at

2022-09-11 20:08:08 UTC

Updated at

2022-09-11 20:08:08 UTC

NP-MRD ID

NP0319215

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione

Description

17-Hydroxy-14-(hydroxymethyl)-16-methoxy-2,6,6-trimethyl-13-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-1(17),10,15-triene-5,12-dione belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. 10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione is found in Swartzia arborescens. 17-Hydroxy-14-(hydroxymethyl)-16-methoxy-2,6,6-trimethyl-13-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-1(17),10,15-triene-5,12-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161516002D          

 27 30  0  0  0  0            999 V2000
    4.6762   -4.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444   -3.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686   -3.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1351   -0.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5486   -0.4095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
  3 27  1  0  0  0  0
 20 27  2  0  0  0  0
M  END


  Mrv1533004161516002D          

 27 30  0  0  0  0            999 V2000
    4.6762   -4.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444   -3.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686   -3.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1351   -0.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5486   -0.4095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
  3 27  1  0  0  0  0
 20 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0319215

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=C(CCC3C(C)(C)C(=O)CCC23C)C2=C1C(CO)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O6/c1-20(2)12-6-5-10-14-15(11(9-22)27-19(14)25)18(26-4)17(24)16(10)21(12,3)8-7-13(20)23/h11-12,22,24H,5-9H2,1-4H3

> <INCHI_KEY>
VFAWCZCJUTVMRS-UHFFFAOYSA-N

> <FORMULA>
C21H26O6

> <MOLECULAR_WEIGHT>
374.433

> <EXACT_MASS>
374.172938557

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.90655202749616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-hydroxy-14-(hydroxymethyl)-16-methoxy-2,6,6-trimethyl-13-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),11(15),16-triene-5,12-dione

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
3.107912353

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.561635033452148

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.739851094042244

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0786680282808616

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
99.21569999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-hydroxy-14-(hydroxymethyl)-16-methoxy-2,6,6-trimethyl-13-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),11(15),16-triene-5,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       8.729  -8.500   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.736  -7.323   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.768  -6.781   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.624  -0.764   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.299  -3.168   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.363  -7.289   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   18                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    6   10   19                                             
CONECT   19   18                                                            
CONECT   20    7   21   27                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24    3   20                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆O₆

Average Mass

374.4330 Da

Monoisotopic Mass

374.17294 Da

IUPAC Name

17-hydroxy-14-(hydroxymethyl)-16-methoxy-2,6,6-trimethyl-13-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),11(15),16-triene-5,12-dione

Traditional Name

17-hydroxy-14-(hydroxymethyl)-16-methoxy-2,6,6-trimethyl-13-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),11(15),16-triene-5,12-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C2=C(CCC3C(C)(C)C(=O)CCC23C)C2=C1C(CO)OC2=O

InChI Identifier

InChI=1S/C21H26O6/c1-20(2)12-6-5-10-14-15(11(9-22)27-19(14)25)18(26-4)17(24)16(10)21(12,3)8-7-13(20)23/h11-12,22,24H,5-9H2,1-4H3

InChI Key

VFAWCZCJUTVMRS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Swartzia arborescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Isobenzofuranone
Benzofuranone
Tetralin
Phthalide
Isocoumaran
Anisole
Alkyl aryl ether
Carboxylic acid ester
Ketone
Cyclic ketone
Lactone
Carboxylic acid derivative
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.83	ALOGPS
logP	3.11	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.74	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.22 m³·mol⁻¹	ChemAxon
Polarizability	39.91 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione (NP0319215)

MOL for NP0319215 (10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione)

3D MOL for NP0319215 (10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione)

3D SDF for NP0319215 (10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione)

3D-SDF for NP0319215 (10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione)

PDB for NP0319215 (10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione)

3D PDB for NP0319215 (10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione)

SMILES for NP0319215 (10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione)

INCHI for NP0319215 (10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione)

Structure for NP0319215 (10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione)

3D Structure for NP0319215 (10-hydroxy-1-(hydroxymethyl)-11-methoxy-6,6,9a-trimethyl-1h,4h,5h,5ah,8h,9h-phenanthro[1,2-c]furan-3,7-dione)